A Singer's Ballad
by TricksieHobbit
Summary: What if, before everything happened to Bobby and Karen, Karen got pregnant and gave up her child? Well thats who Roy Singer is! This story takes place in season 9.
1. Chapter 1: A Singer in the Dark

Chapter 1

A Singer in the Dark

He sat alone in a corner booth. The diner only contained a few others, sketchy people that you would not want to be alone with. Having no other choice he sat there alone. His dimly blue eyes fixed on the door like a guard watching their prisoner. Anxiously he fidgets running his hand through his dark blond, verging on brown, hair. Glancing down to see the time he hears the chimes of the door. Instantly looking up, seeing two men around his age enter the diner. The taller one had long wavy brown hair down to his shoulders wearing a plaid shirt and blue jeans. The one that looked to be his own height had much shorter brown hair, like the man in the booth but a tad shorter, and also had a stubble. He looked up them, hoping that these were the men that knew the answers he was searching for. They looked around for a moment noticing him staring. They exchanged a few words, out of his earshot, and then approached him. "Are you Roy?" questioned the shorter one the man nodded and spoke "You the Winchesters?" The tall one replied as he joined the man in the booth "Yeah, you wanted to know about Bobby Singer?" the shorter one barged in "Why do you wanna know about Bobby?" "Hes my Father."

"Wait Bobby had a son?" Dean questioned as he sat. "Yeah that's kinda how I'm here right now" "Bobby never talked about you. How do we know you are who you say you are and not say a demon or worse one of those angel dicks?" Roy sat there taken back by what he had just said "What?" Sam chimed in "I think that means he doesn't know what we are talking about Dean." again Roy questioned "What do you mean a Demon or an Angel? Are you guys okay?" In a furry Dean bantered "No we are not okay! You just told us that one of our closest friends had a son and never told us squat about him" Sam soothed "Dean, maybe he didn't know. Maybe Karen knew how adamant Bobby was about not wanting to have a kid and dealt with it" "I'm right here. Just talk to me." "Dean, Bobby would want us to leave him alone. To give him a normal life" "What are you two talking about!? What do you mean normal life?" "Roy, just let it be. Your father was a good man and a good friend. You don't wanna get messed up with us. Leave go live your life the way he would want" The two brothers start to leave. Roy gets up after them "I don't know how he'd want me to live." Dean looked back in a sense of understanding. He motioned for Roy to follow. As Roy paid for the coffee he'd been nursing Sam questioned Dean "He has the chance for a normal life. Why not let him have it?" Looking back to Roy seeing how he had gone through most of his life not knowing his family "We are the closest things he has to family"

The Winchesters weren't completely convinced of his innocence. So they brought him to the middle of nowhere. As they come to a stop Roy pipes up "Where are we?" The brothers got out of the impala. "Get out" Dean grunted before closing the door. Roy felt unnerved, they were all alone and for all he knew these men had killed his father. Cautiously he exited the car, a brother on either side of him "Answer me dammit! Where are we?!" A sharp pain suddenly made its presence on the back of his neck. "What the hell!" He yelped as his hand raced to protect opening. "A precaution" then the other brother threw water in Roy's face. "I repeat! What the hell!" "And I repeat a precaution" "Precaution for what?!" "Wanna make sure you are who you say you are" "I have ID" He reaches for his wallet as Sam cuts himself and starts to draw with his blood. Dean laughed "We don't mean like that" "How did you know my father? Was he crazy like the two of you?" As Sam finishes the sigil he places his bloody hand on the center. Nothing happens. Sam sends a look Dean's way. "Okay you're clean. Bobby was a Hunter." A little relieved and a little confused Roy responded "All this and he was a hunter?" "Not that kind of hunter" Dean informed. "Dean, are you sure?" Sam again rose the question of telling the wayward Singer about his father. "He deserves to know about his father Sam! He hunted things. The things regular people don't believe are real. Like Monsters and things that go bump in the night. They are all real Roy. That's the reality of the world we live in. You either know and you hunt or you know and you hide." After a moment of sinking in what Dean had said Roy began "and my Dad, Bobby Singer, He hunted these things? And you too?" Dean and Sam nodded. "Is that how he died?" "Bobby was a good guy. He went down fighting" "What about my mother? Was she a hunter too?" "No. Shes actually the whole reason he got roped into this mess." "What do you mean?" "Let's just say her death wasn't natural…" he stands, taking in all this information about his family, in the silence of the woods with the Winchesters.

As the Winchesters drive Roy sits in the back seat staring out the window. The road is dark; all that can be seen are the trees that seem to race past. Racing past the way he felt his life was going by. He just learned the whole truth about his family. Now he was completely afraid and without family. He glances to the front seats, where the Winchester brothers sit, and ponders why did his father love these two as his own when he had a son he abandoned? Roy looks back to the window. What would he do now? His whole life has been devoted to finding the family that had abandoned him. Now he had found out about the supernatural how could he ignore it? After a while of driving they stopped in front of the diner where they had met. "Well Roy, you wanted to know about Bobby. You got to know." Dean spoke up. Roy looked out to the diner, it was dingy and unclean. He had a choice. On one hand he could go with the Winchesters and learn more of his Father. On the other hand he could return to a normal life and start his own family. Dean proclaimed "Come on Roy we don't have all night." After a moment more of thought Roy replied "May I go with you? I would like to become a hunter" A little startled Dean questioned "Come with us? Are you sure?" "Yeah, I am." "Okay. Just so you know it's not a walk in the park. You could die" he discouraged. Roy breathed "Don't try to talk me out of it. I haven't done anything with my life so far. So why not become a hunter?" "Okay" the two brothers had been convinced. Dean began to drive off, the Impala containing the two sons of John Winchester and the abandoned son of Bobby Singer.

On the long and seemingly interminable drive Dean and Sam were informing Roy about all the routines and precautions that come with the job. They had told him that making a ring of salt then standing in it will protect you from ghosts and other things. Most Angels are as bad as Demons, even though they are told to be loving pure beings. Hearing all this information was overwhelming and Roy wondered if this was the best decision. What if I do something wrong and cause someone to die? I couldn't handle that. The Winchesters seem to have an unlimited amount of knowledge regarding the supernatural. Listing everything from Angels to Wendigos. Roy just sits in the backseat of the impala soaking it all in, trying not forget all they say.

Suddenly someone was on the road. Dean slammed his foot on the brakes yelling out of shock. Sam braces himself by grabbing the dashboard. Whereas Roy braces himself on the back of Dean's seat. The figure vanished just before were about to come into contact with it. Dean and Sam look around to see if it will reappear. Roy starts have a mini melt down "What was that?!" "Well I'm not sure could've been a ghost or an angel. Basically one of the many things we just told you all about. Looks like you might get to test out what we just taught you" Dean laughs in response. The Winchesters emerge from the Impala and head towards the trunk. Roy is sitting in the back seat is looking outside with great caution. He thinks for a moment that he hears something that sounds like wings. Turning to look to his right he sees someone sitting next to him. He jumps with a fright, not because the man next to him is scary, because he believes he knows this man. "Jason?" Jason is around the same height as Roy, same age as well. His hair is black and tangled as though he had just woken up. His eyes glimmered with green. Before he turned to look to Roy his profile revealed he had a nose that usually belonged to snobs. "What are you doing here?" His friend turned to him "I'm not Jason. I'm Zadkiel, Angel of the lord" "What?! You're an Angel?" "Yes. Where are the Winchesters?" Without realizing Roy looked back to the trunk revealing there position. When he looked back Zadkiel was gone.

The two brothers were rummaging through the trunk grabbing salt, holy water, an angel blade left by Castiel, when Zadkiel appeared before them "You are the Winchesters?" Dean shot up and addressed Zadkiel "Who the hell are you?!" "I'm Zadkiel, Angel of the Lord" Dean, still holding the Angel blade, lunged to attack Zadkiel. Dodging seemed to come easy to him, every attempt Dean made to hit him Zadkiel would evade. Roy bursts out of the car to see whats going on. Sam walks over to Dean and puts his hand on his shoulder "Dean, this Angel is good. I do not believe he means us any harm or any harm to Castiel" Dean looked up to the man that was not his brother but an Angel and lowered his weapon. Zadkiel looks strangely at Ezekiel almost as though he was trying to remember him. "You are an Angel?" Ezekiel looked to Zadkiel and relinquished control back to Sam. Zadkiel acknowledged the change as though he understood not to say a word. "Okay Zadkiel. You're a good Angel that means us no harm. What do you want with us? Wait and while we are asking questions how did you find us?!" "I have been waiting and watching Roy Singer in case he ever tried to find out about his family. It seems to have been a good idea" Dean looks over to Roy. "You were Angel bait?" "I didn't know!" "He only knew me as my vessel, Jason Loomis" "What do you want with us if you're not bad?" "What makes you think hes not bad Dean?" "Well he hasn't zapped us anywhere or killed us, so my moneys on hes not trying to kill us" "I want to help Castiel. He was a good friend of mine before all this happened and I can't find him" Dean looks down "Cas is gone" He looks up to Zadkiel "I don't know where he is" "I don't understand. I thought-" Dean argued "You thought wrong" then in a moment the sound of wings and Zadkiel was gone. "Is that a normal kind of occurrence?" Dean and Sam look back to Roy after he burst out. Dean responds with a mixture of facial expressions and words "yeah it seems to be getting there" The three of them get into the Impala and drive off.

After hours of driving they arrive at a large bunker door. The brothers get out of the Impala quickly followed by an overwhelmed Roy. "Here we are home sweet home" Dean announced as he headed for the door that was down a staircase. Before Sam followed he looked to Roy "How are you holding up? I know this is a lot to take in" "I should be fine. I guess you're not a hunter until your best friend becomes an Angel" "Haha yeah" The two follow Dean down the staircase and enter the bunker. "Home sweet Home" Roy muttered.


	2. Chapter 2: A Man of Letters to be

Chapter 2

A Man of Letters to be

Roy woke up in a bunker room. The room was grey; it seemed to be decorated in the 30's style. Lying on a rather comfy bed he reflects on everything. His best friend from the orphanage he was raised in was now possessed by an Angel. His father hunted supernatural creatures and that's what led to his death. Roy's world was now completely different, even though nothing has changed other than his knowledge of these things. All he could think was this would now be his life. As he lay there he heard Sam and Dean, the walls are thick so their voices are muffled. Roy takes that as a cue to wake up, so he swings his legs off the bed while also throwing the sheets off himself. He sat for a moment, a little light headed caused from sitting up to fast, wearing blue, plaid pyjama pants and a men's grey, tank top covering his slight build of a body. Now, looking to the door, he starts to leave. When Sam passes the door "Sam! Hold up a moment!" Roy exclaims heading swiftly to the door. Sam stops outside Roy's door "Oh hey Roy, We uh, we didn't know you were up yet" "I have to admit that bed was incredibly comfy I almost didn't want to get up" Roy meets up with Sam at the door "Yeah memory foam its great" they turn and head down the hallway "Anyway Sam, I was wondering if I could look through some of those books I saw when I came in. I like to read" Roy asked inquisitively. "Uh sure, no problem. Just uh, one thing, they might be a little strange they were written by men of letters. They were basically like scholars of the abnormal" "Wow so there has been a whole conspiracy about the supernatural since the 30s'?" "Well even before that actually. Hunters go back for as long as people have been writing down history. Probably even further back then we will ever know" Roy thought in wonder "and to think most people on this planet no nothing of it" Sam chimed in "or they choose to ignore it". As they reach the end of the hall they enter the main room. The room is grand filled with shelves of books. In the middle of this section of room sits three square tables, in a row, with four chairs at each one, two on the left two on the right. The next section of room has an elaborate table with a map and light system built into it with a few chairs placed around. Also in that section a staircase that leads up to the second level where there is a place to play chess and exit the bunker. "Enjoy your reading Roy. Dean and I have a job to go do in Oklahoma" "Would you like me to assist?" "We'll be fine. You stay here and do you're research on our line of work" Dean enters the room "Roy. Enjoy that memory foam? Its great isn't it?" Roy chuckles "Yeah it's great. I hear you two are going on a hunt" "Yeah something that I could probably handle on my own. Just stay here Sam, I've got this" "No Dean, we already discussed this I'm going" "fine," Dean succumbs then finishes "well see you after we get back" Dean and Sam head up the stairs towards the exit. "Oh and Roy, friendly advice don't eat Dean's pie" "You better not eat my pie!" "I won't eat your pie. I promise" with that the brothers left leaving Roy alone in the Bunker of Letters.

The Winchesters had been gone an hour, Roy had showered and dressed. He returned to the main room finding it awkwardly empty. He starts rummaging through all sorts of strange books; Roy read and consumed knowledge of all sorts of creatures. As he picks up a hunters journal a photo falls out, in the photo are Sam, Dean and an older man wearing a ball cap and plaid. He had short brown hair and a short brown beard with small amounts of grey hair. When he turned it over the back read Bobby, Dean and Sam. This was a photo of his father. He turned the photo over to see him again. Now looking at his father he felt saddened to have never met him. In Roy's moment of sadness he heard his phone start to ring. Jamming the photo into his pocket with one hand while the other searched for the phone. "Oh come on! Where is it?!" finally he found his phone, it had fallen to the ground during his inspection of the books. "Hello?" he greets the person on the other end a tad out of breath. "Roy?" the mysterious voice replied. "Yeah that's me" "Its Jason. I need your help. I think I got really wasted last night and so I woke up in Lebanon, Kansas. And you know me; I hate Kansas" annoyed Roy responds "Where exactly are you?" "Uh a gas station. Listen I know you said that if this kind of thing ever happened again, I shouldn't go running to you for help but I have the strangest feeling I saw you last night" Roy stay silent for a moment and awkwardly chuckles "Yeah, that is strange, Okay well I'll be on my way soon. Lucky for you I'm in Lebanon right now" "Thank god! I would hate to stay in this dump any longer" not directed at Roy "No offense. Wait offense! This is an awful red neck dump!" back to Roy "Okay I think I just made an enemy if you would hurry that would be great" Roy hears the phone drop and Jason's voice "You don't wanna fight me! I'm half your size. Well he's my size but he doesn't wanna fight me either!" Roy then hangs up the phone. Roy thought to himself _why does he always get himself into trouble?_ Roy heads down to where the brothers had told him there was a ride if he needed to go to town. He enters a long hanger full of old school bikes and cars. After a moment of standing in awe he heads straight for the light green one with a white roof. Looking through the car for keys he finds them hiding in the glove box. Once the car starts off Roy drives off headed to town.

After a while of driving Roy came upon a gas station. As he pulled up he noticed Jason was getting beaten up by large Biker and a smaller biker the same size of Jason, which was rather skinny. He parks and runs over to save his friend. "Hey! Leave him alone!" The smaller biker stops and looks up at his friend. "And why would we just listen to you?" The big biker comments acting rather tough. "Because I called the cops and they are on their way right now to arrest you for assault" the two bikers look to one another. The smaller one panics "should we believe him?" "It'll be our third strike if it's the truth" the big one answered. The two bikers then ungracefully retreat to their bikes and drive off swearing like sailors. Jason lay on the ground eyes shut, bruised, beaten and whimpering. "Jason, are you okay?" Jason opens one eye and looks up to Roy. "I'm fine. This is why I hate Kansas! No one knows how to take a joke!" Roy looks down at his friend who last night he saw was the exact opposite of the man at his feet. Jason was a wimp, a drunk, an idiot and a womanizer. The angel that possessed him seemed to be the polar opposite. Roy reached his hand out to his friend, Jason welcomed the help up. Now they stood Jason just a tiny amount shorter then Roy. Roy Preached "You really need to stop drinking" "No, I need to drink more to get less drunk" "Jason, did you get drink this morning?" "No..." Roy stares at him in disbelief "just the little drink I shared with those guys before they beat me up" "You have a problem" "You have a problem!" Jason then passed out falling on Roy. He stumbled now holding up his drunken, beaten and possessed friend. Trying his best to drag his passed out friend to the car he had shown up in. When Jason suddenly woke up and stood upright, more upright then Roy had ever seen. "Roy, Good to see you again. I am sorry for confusing your friend" "Um, Jason…" "I realize this must be awkward for you. Remember me Zadkiel?" "Right, you are possessing Jason" "All of this was agreed to by Jason. Being an Angel I need the permission of the vessel. I truly feel awful about using him in this manner. I am the Angel of Free Will, so you must understand me when I say I feel terrible about taking it away" "I was told Angels are bad. That I shouldn't talk to them" "Most of us merit that response. There are a group of us that wish to help Castiel. We know this was not his intent and want to help him evade Bartholomew" "I don't know anything about this Castiel I keep hearing about" "Some like to think of him as the Winchesters Guardian Angel. I hate to keep Jason from his sleep. If you learn anything of Castiel's whereabouts pray to me." Zadkiel enters the car lies down and releases control allowing Jason to sleeping. Roy looks towards the car and thinks _Can I Trust him? Did he pick Jason to trick me? Or is he really a good angel?_

Roy drives to a diner; it's more of a family breakfast diner then the grungy place where he met the Winchesters. Looking to the back seat he sees Jason still sound asleep. Quietly Roy searches for a pen and paper. When finally after searching through all sorts of old hunters equipment he comes across what he was searching for. Writing down a note then placing upon his friend's chest. The note reads: In the Diner, join me for breakfast. After finishing with the note he silently leaves the car. Approaching the diner he looks to the sky and thinks to himself _it used to be so simple, the sky was a part of the atmosphere beyond that was space then more planets for light years. Now there is heaven and hell. All religions have a part of this puzzle we call life._ He finishes his thought as he enters the small family diner. Sitting inside are a few families eating their meal peacefully, well as peaceful as one can with a family. Roy proceeds to a booth away from the families. A waitress heads over to greet him after a moment of sitting. "Hello I'm Jacqueline and I will be your waitress today." The girl looked to be in her twenties; Strangely enough she did not have a southern accent. She had dark brown hair up in a ponytail. Her eyes were also a deep brown accenting her slightly tanned skin. She seemed to stand a few inches shorter then Roy. "I'm Roy. Nice to meet you Jacqueline." "May I take your order?" Roy looks down at the menu. "I think I would like to try your Bacon and eggs special, and a coffee" "Would you like anything else with that?" Roy looks to the car "Actually make that two coffees and two specials, I'm waiting for my friend" "Alright, I will be back with your order" The girl walked away with a prance in her step. Roy sits patiently waiting.

After waiting for a while Jason stumbles into the Diner. Roy looks up to him, raising his hand to convey where he is. His hung over friend shuffles over, the families sitting throughout the diner look at him in disgust. Just as Jason sits down the waitress arrives with their coffee, instantly putting in on the table. "Here you are. And Roy this must be your friend." She reaches out her hand to Jason "Hi I'm Jacqueline" Jason looks up to the girl instantly smitten. "Well hello there Jacqueline. My name is Jason" Jacqueline smiles as Jason kisses her on the hand. As she starts to walk away he keeps his hand under hers and slowly released it as she got too far away. After a moment Jason looks back to Roy "Sweet girl" "Do you have to act that way about every girl you come across?" "I don't hear any complaints from them" In the middle of their discussion she comes back bringing with her their breakfast. "Thank you darling" She smiles then heads off with a spring in her step. Roy and Jason then eat their freshly cooked breakfast. As Roy eats he can't help but feel that something is off.


End file.
